Hydrochloric Acid → Phenylthioethanethiol

HRID 223653Notes

Reaction equation

HRID 223653 reaction equation
[C:1]1([S:7][CH2:8][CH2:9]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1([SH:17])C=CC=CC=1.C1OC1.[OH-].[K+].NC(N)=S.Cl.O.NN>C1(C)C=CC=CC=1>[C:1]1([S:7][CH:8]([SH:17])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 6354Ethylene OxideHCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 696852-(Phenylthio)ethanolHCID 2723790Thiourea

Product 1

HCID 23503969Phenylthioethanethiol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

77 g of 2-phenylthioethanol, (0.5 mol, prepared from thiophenol and ethylene oxide in the presence of some potassium hydroxide) are maintained for 4 hours under reflux with 40 g of thiourea and 50 g of 37% hydrochloric acid. At 40° C., the reaction mixture is stirred with 50 g of 50% hydrazine hydrate solution for 30 minutes. 100 ml of toluene are added, this is maintained for 30 minutes in the steam bath, the toluene phase is separated off and compressed under vacuum.

Workup

  1. temperatureare maintained for 4 hours
  2. temperaturethis is maintained for 30 minutes in the steam bath
  3. customthe toluene phase is separated off

Sources & evidence

ORD record
ord-cf8da0c2aaf54b18a49b46c8662c59e6
Source dataset
uspto-grants-1982_10
Patent number
US04355185

Reaction notes

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